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Preparation method of lenalidomide

A technology of lenalidomide and compounds, which is applied in the field of drug synthesis, can solve the problems of iron sludge difficult to filter and iron ion contaminated products, and achieve the effects of reducing production costs and cycles, facilitating industrialized production, and realizing industrialized production

Active Publication Date: 2017-07-18
CHANGZHOU PHARMA FACTORY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has the advantages of low cost and environmental friendliness, but the iron sludge produced by reduction is difficult to filter, and it is easy to introduce iron ions to pollute the product

Method used

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  • Preparation method of lenalidomide
  • Preparation method of lenalidomide
  • Preparation method of lenalidomide

Examples

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Embodiment 1

[0030] Preparation of 3-(4-nitro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione (I):

[0031]

[0032] Add 99.9g of 2-bromomethyl-3-nitrobenzoic acid methyl ester, 50.0g of 3-amino-2,6-piperidinedione hydrochloride and 96.6g of sodium carbonate to 500ml of tetrahydrofuran, heat to reflux for reaction, HPLC Stop the reaction when it detects that 3-amino-2,6-piperidinedione hydrochloride is less than or equal to 0.5%, cool the reaction solution to room temperature, pour the reaction solution into 2L purified water, stir at room temperature for 1 hour, filter, and the filter cake is dispersed in In a mixture of 1L ethanol and 1L purified water, stir at room temperature for 1 hour, filter, disperse the filter cake in 1L ethanol, stir for 1 hour at room temperature, filter, wash the filter cake once with 200ml ethanol, and dry the filter cake at 50°C for 10 Hours, 80.8 g of an off-white solid was obtained, with a yield of 92.0%. 1 HNMR (DMSO) δ11.03(S, 1H), 8.46(dd, 1H...

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Abstract

The invention relates to the field of drug synthesis, and particularly relates to a preparation method of a lenalidomide intermediate and lenalidomide. The compound is a drug for treating multiple myeloma. The method comprises the steps of adopting 2-bromomethyl-3-nitrobenzoate and 3-amino-2,6-piperidione hydrochloride as reaction substrates and an inorganic base as an acid-binding agent and obtaining a white to almost white key intermediate 3-(4-nitro-1-oxo-1,3-dihydro-2H-isoindole-2-yl) piperidine-2,6-diketone of the lenalidomide through simple post-treatment; and adopting a mixed solvent of an organic solvent and water as a reaction solvent and carrying out catalytic hydrogenation in the presence of palladium on carbon to prepare the lenalidomide (II). The process route is low in production cost, and a product is high in purity and friendly to environment, and has relatively great implement value and social and economical benefits.

Description

technical field [0001] The invention relates to the field of drug synthesis. It specifically relates to the key intermediate 3-(4-nitro-1-oxoisoindol-2-yl)piperidine-2,6-dione and its compound for the treatment of multiple myeloma drug lenalidomide A novel preparation method of lenalidomide. Background technique [0002] The chemical name of lenalidomide is 3-(4-amino-1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione ( II) was developed by the US Cell Gene Company and was approved by the US FDA for marketing in January 2006. The drug is used to treat myelodysplastic syndrome (MDS) subtypes with 5q deletion (a gap gene deletion on the long arm of chromosome 5) and multiple myeloma. The structural formula of lenalidomide is as follows: [0003] [0004] 3-(4-nitro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione (I) is a synthetic lenalidomide (II ) important intermediate, the structural formula is as follows: [0005] [0006] Fang Feng, Xu Xu, Ji Yaf...

Claims

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Application Information

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IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 马贯军巫美金
Owner CHANGZHOU PHARMA FACTORY
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